IP Library › Granted Patent US 9,647,217
Granted Patent B2
US 9,647,217 · App. 14/188,297 · Granted May 9, 2017

Organic electroluminescent materials and devices

Inventors: Chun Lin (Yardley, PA); Lichang Zeng (Lawrenceville, NJ); Chuanjun Xia (Lawrenceville, NJ)
Assignee: Universal Display Corporation
H01L51/0072C07D409/14H01L51/0071H01L51/0074H01L51/5016
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Quick Facts
Patent No.
US 9,647,217
App. No.
14/188,297
Granted
May 9, 2017
Kind
B2
Abstract

The present invention relates to novel organic compounds comprising at least two different selections selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene. The compounds are useful for organic light-emitting diodes. The compounds are also useful for charge-transport and charge-blocking layers, and as hosts in the light-emissive layer for organic light emitting devices (OLEDs).

Claims (51)

1. A compound having formula I:

A-L-B  (I);

wherein A and B are each different selections selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene;

wherein A and B can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein two adjacent substituents can optionally join to form a fused ring;

wherein L is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, and substituted cycloalkyl; and

wherein L can be substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

2. The compound of claim 1 , wherein A including optional substituents and B including optional substituents are different.

3. The compound of claim 1 , wherein the compound further comprises C;

wherein C is selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene;

wherein C can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein C is connected to A or B by L′; wherein L′ is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, and substituted cycloalkyl; and

wherein L′ can be substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

4. The compound of claim 3 , wherein C is a different selection from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene than A and B.

5. The compound of claim 3 , wherein A, B, and C have no further substitution.

6. The compound of claim 3 , wherein no more than one of A, B, and C is aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, or aza-triphenylene.

7. The compound of claim 3 wherein L′ has from 1 to 24 carbon atoms.

8. The compound of claim 3 , wherein L′ is selected from the group consisting of

and wherein the dash lines represent a direct bond between L′ and C, and L′ and A or B.

9. The compound of claim 3 , wherein the compound is selected from the group consisting of:

wherein X is O or S;

wherein X 1 to X 16 , Y 1 to Y 26 , and Z 1 to Z 24 are each independently selected from the group consisting of CR and N; and

wherein R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein two adjacent R can optionally join to form a fused ring.

10. The compound of claim 1 , wherein A and B have no further substitution.

11. The compound of claim 1 , wherein A and B are each independently selected from the group consisting of N-phenyl carbazole, aza-(N-phenyl carbazole), dibenzofuran, dibenzothiophene, and triphenylene.

12. The compound of claim 1 , wherein A is selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, and triphenylene; and B is selected from the group consisting of aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene.

13. The compound of claim 1 , wherein L has from 1 to 24 carbon atoms.

14. The compound of claim 1 , wherein L is selected from the group consisting of

and wherein the dash lines represent a direct bond between L and A, and L and B.

15. The compound of claim 1 , wherein A or B is (9-carbazolyl)-(N-phenyl-carbazole).

16. The compound of claim 1 , wherein the aza-(N-phenyl carbazole) is selected from the group consisting of N-pyridyl carbazole, N-pyrazinyl carbazole, and N-triazinyl carbazole.

17. The compound of claim 1 , wherein the compound is selected from the group consisting of:

wherein X is O or S;

wherein X 1 to X 8 , Y 1 to Y 13 , and Z 1 to Z 12 are each independently selected from the group consisting of CR and N; and

wherein R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein two adjacent R can optionally join to form a fused ring.

18. The compound of claim 1 , wherein the compound is selected from the group consisting of compound 1 to compound 459 listed below:

19. The compound of claim 1 , wherein A is dibenzothiophene, L is —CH 2 —, and B is N-phenyl carbazole.

20. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having formula I:

A-L-B  (I);

wherein A and B are each different selections selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-carbazole, aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene;

wherein A and B can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein L is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, and substituted cycloalkyl; and

wherein L can be substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

21. A formulation comprising a compound having formula I:

A-L-B  (I);

wherein A and B are each different selections selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-carbazole, aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene;

wherein A and B can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein two adjacent substituents can optionally join to form a fused ring;

wherein L is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, and substituted cycloalkyl; and

wherein L can be substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 11, 2014
From: LIN, CHUN; ZENG, LICHANG; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 033293/0302 →
Continuity (1)
Related Publication 20150243904A1 · Aug 27, 2015